Surface Activity of Alkoxy Ethoxyethyl β-d-Glucopyranosides.

Dioxyethene fragment (-(OCHCH)-) was introduced into traditional alkyl β-d-glucopyranosides to ameliorate the water solubility, and eight nonionic surfactants, that is, alkoxy ethoxyethyl β-d-glucopyranosides with alkyl chain lengths ( = 6-16), were synthesized and characterized. Their hydrophilic and lipophilic balance number, water solubility, critical micelle concentration (cmc), γ, Γ, and hygroscopic rate decreased with an increase in the alkyl chain length. Hexadecoxy ethoxyethyl β-d-glucopyranoside had no water solubility at 25 °C. Decoxy ethoxyethyl β-d-glucopyranoside had the best emulsifying property in the toluene/water and -octane/water systems and the strongest foaming property, whereas dodecoxy ethoxyethyl β-d-glucopyranoside had the best emulsifying property in the rapeseed oil/water system. Such β-d-glucopyranosides ( = 6-12) exhibited excellent surface activity. In addition, for the binary mixture of alkoxy ethoxyethyl β-d-glucopyranosides ( = 8, 10, 12) and sodium dodecyl sulfate or cetyl trimethyl ammonium chloride, their cmc values were lower than the pure β-d-glucopyranosides, indicating that they had synergistic interactions. The fan focal conic textures of alkoxy ethoxyethyl β-d-glucopyranosides ( = 7-16) were observed during the cooling process under a polarizing optical microscope. Alkoxy ethoxyethyl β-d-glucopyranosides ( = 14, 16) had the related melting points and the clear points with differential scanning calorimetry. With β-d-glucopyranosides ( = 6-16) and -butanol as the surfactant and cosurfactant, respectively, and with cyclohexane as the oil phase, the related microemulsion areas in their pseudoternary phase diagram system were investigated with the visual observation at 25 °C. Along with the slashing requirements of petroleum consumption, environmental protection, and green and sustainable development, nonionic sugar-based alkoxy ethoxyethyl β-d-glucopyranosides should be expected to have their potential practical application because of their strengthened hydrophilicity, improved water solubility, and enhanced surface activity.